$26 Cheap Flights to Chicago, IL

View $26 flight on Wed, Mar 11, 2026Opens in a new window

Popular airlines to Chicago

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Today's featured flight deals to Chicago

Nonstop
Carry-on included
Lower price than typical

How much is the cheapest flight to Chicago?

Prices were available within the past 7 days and start at $26 for one-way flights and $52 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, Apr 28 - Wed, Apr 29
IAH
Houston
ORD
Chicago
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Apr 28 from Houston to Chicago, returning Wed, Apr 29, priced at $56 just found
Spirit Airlines
Sat, Apr 18 - Sat, Apr 25
IAH
Houston
ORD
Chicago
$66 Roundtrip, just found
$66
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Apr 18 from Houston to Chicago, returning Sat, Apr 25, priced at $66 just found
American Airlines
Sat, May 2 - Wed, May 6
BOS
Boston
ORD
Chicago
$112 Roundtrip, found 13 hours ago
$112
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, May 2 from Boston to Chicago, returning Wed, May 6, priced at $112 found 13 hours ago
Delta
Sat, May 2 - Tue, May 5
BOS
Boston
ORD
Chicago
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Delta flight, departing Sat, May 2 from Boston to Chicago, returning Tue, May 5, priced at $117 just found
United
Sat, May 2 - Tue, May 5
BOS
Boston
ORD
Chicago
$117 Roundtrip, just found
$117
Roundtrip
just found
Select United flight, departing Sat, May 2 from Boston to Chicago, returning Tue, May 5, priced at $117 just found

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $417
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $417
Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $257
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $257

Find the cheapest month to fly from Columbus (CMH) to Chicago (CHI)

August is typically the cheapest month to fly

From $85 - $364 per traveler.

Chicago Flights

Chicago Airports

When youíre looking to book flights to Chicago, Illinois, there are two airports that serve the Windy City. O'Hare International Airport is the main one, while Chicago Midway International Airport is considered the secondary tarmac.

O'Hare sits 17 miles northwest of the Loop. It provides plenty of amenities to keep you entertained while you wait for your flight or transportation into Chi-Town. If youíre hungry, youíre in luck. This airport boasts a variety of restaurants and cafes, providing sit-down cuisine and meals-on-the-go. The airport also features various shops, where you can find Chicago souvenirs, designer goods, electronics, and duty-free products. To top it all off, O'Hare provides spa services and even a yoga room to help keep you relaxed and rejuvenated during your travels.

Located roughly 12 miles northwest of downtown Chicago, Midway Airport includes several shops, the majority of which are located in the Midway Boulevard. You can also find restaurants, snack shops, and fast-food options when youíre looking fuel up before or after your flight. While youíre traveling through the airport, look for the public art and installation collections throughout the terminal.

Airport Transportation

When you have Chicago flights, rest assured knowing that both airports provide ground transportation. Here at Expedia.com, you can reserve Chicago car rentals and pick up your vehicle at your preferred airport. Alternatively, you can take advantage of public transportation as the Chicago Transit Authority provides both train and bus service to Midway and OíHare. Other transportation options include taxis, shuttles, and limousines.

Chicago Activities

Once youíve decided itís time to book plane tickets to Chicago, IL, start planning your adventures. The Windy City is home to fascinating exhibits, from the galleries at the Museum of Contemporary Art to the artifacts at the Chicago History Museum. For some of the best views of the skyline, venture up to the 360 Chicago observatory deck in the John Hancock building or the Skydeck Chicago in the Willis Tower. While youíre in town, chow down on some famous deep-dish pizza or Chicago-style hot dogs for an authentic taste of the city. Then round out your day with reservations at one of the best hotels in Chicago.

Planning Your Trip

The best times to visit Chicago are between April and May and September and October. Temperatures are moderate during these months, and the high season hasnít hit yet. Summertime is considered the most popular time to visit, so you may face more crowds and more expensive rates during this season. Meanwhile, winter brings temperatures in the low 30s F and a high chance of snowstorms.

Regardless of when you plan to visit, Expedia.com is here to match you with cheap flights to Chicago. Sort through our selection to find discounts on round-trip tickets that suit your price range. You can even use our mobile booking app for convenient access to exclusive online deals on airfare to Chicago. Book your affordable flights right here and start getting a taste for that delicious deep-dish pizza.

Frequently asked questions

What month is the cheapest to fly to Chicago?
September is the cheapest month to fly to Chicago, with average fares around $404. This month often has lower demand, which helps keep prices down. You can also find good deals in January, February, and April.*Prices based on flights available on Expedia in the last year.
Which US cities have the cheapest flights to Chicago?
Looking for affordable flights to Chicago? Consider flying from these US cities:

  • Burlington (BRL, BTV)
  • Quincy (UIN)
  • Owensboro (OWB)
  • Kirksville (IRK)
  • Manistee (MBL)

with prices usually starting around $39.
How to find a cheap flight to Chicago?
To find a cheap flight to Chicago, be flexible with your dates. Traveling in the off-season or shoulder season can help you save. Mid-week flights are usually less expensive, too. Use flight search engines, like Expedia, to compare airlines, flight times and routes all in one place to find affordable rates. You may find that flights with layovers are cheaper than direct flights. You can also set up Price Tracking and receive alerts when fares go up or down.
Which airlines fly to Chicago?
Multiple carriers fly to Chicago:

  • American Airlines
  • Delta
  • Frontier Airlines
  • Spirit Airlines
  • United
  • United Airlines
  • Volaris

Where do you fly into Chicago?
If you're heading to Chicago, you have several airport options:

  • The closest major airport is Chicago, IL (ORD-O'Hare Intl.), about 20 miles from the city center, which is a hub for United, American Airlines, and Delta, with other airlines like Frontier Airlines, Air Canada also operating here.
  • Milwaukee, WI (MKE-General Mitchell Intl.) is another option, about 76 miles away, serving as a hub for United, Delta, and WN, with American Airlines, Alaska Airlines also operating here.
  • Chicago, IL (MDW-Midway Intl.), about 10 miles away, serving as a hub for WN, Delta, and Frontier Airlines, with Volaris, Porter Airlines also operating here.
  • South Bend, IN (SBN-South Bend Intl.), about 92 miles away, serving as a hub for United, American Airlines, and Delta, with MX, OO also operating here.
  • Kalamazoo, MI (AZO-Kalamazoo-Battle Creek Intl.), about 145 miles away, serving as a hub for Delta, American Airlines, and United, with MQ, OO also operating here.

Which budget airlines fly to Chicago?
For budget travel to Chicago, there are 13 low-cost airlines to choose from, including:

  • Southwest Airlines: serves Chicago (MDW), Milwaukee (MKE), Chicago (ORD)
  • Spirit Airlines: serves Milwaukee (MKE), Chicago (ORD)
  • Frontier Airlines: serves Chicago (MDW), Milwaukee (MKE), Chicago (ORD)
  • Volaris: serves Chicago (MDW), Chicago (ORD)
  • JetBlue Airways: serves Milwaukee (MKE), Chicago (ORD)
  • Viva Aerobus: flies to Chicago (ORD)
  • Sun Country Airlines: serves Milwaukee (MKE), Chicago (ORD)
  • WestJet: serves Kalamazoo (AZO), Chicago (MDW), Milwaukee (MKE), Chicago (ORD), South Bend (SBN)
  • Breeze: flies to South Bend (SBN)
  • Arajet: flies to Chicago (ORD)

What is the best month to visit Chicago?
The best month to visit Chicago depends on your priorities, whether you want ideal weather, fewer crowds, or the lowest prices. If affordability matters most, look for cheap April flights outside of peak season.
How far in advance should I book a flight to Chicago?
It's usually cheaper to book flights to Chicago a few months in advance. For added peace of mind, use Expedia's Price Drop Protection™ when you make your booking. It's free to use for Gold and Platinum members on the Expedia app. Once a qualifying flight is purchased, we'll automatically check your flight on Expedia until the day of your departure and notify you if there are price changes. If your flight price drops after you book, we'll automatically award the price difference in OneKeyCash™* into your One Key account after your trip ends.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What day of the week is cheapest day to buy a plane ticket to Chicago?
Saturday is typically the cheapest day to buy a plane ticket to Chicago, averaging about $398. This is beneficial for travelers since Monday is usually the most expensive day. Use Expedia's Price Tracking tool to monitor prices for your trip and receive alerts when fares go up or down.*Cheapest day to book based on flights available on Expedia in the last year.
What is the most expensive month to fly to Chicago?
July is the most expensive month to fly to Chicago, with average return ticket prices around $472. This is about 7% higher than the average throughout the past year, as summer travel peaks during this time. For better deals, consider traveling in September or October.*Prices based on flights available on Expedia in the last year.
How can I track flight prices to Chicago?
Our Price Tracking tool allows you to monitor fares to Chicago. You can view flight price history and see predictions of future prices as available. When you're signed into your Expedia account, you can set up flight price alerts too. This way, you'll receive notifications when prices go up or down, so you know when it's the right time to book.
How to get a cheap last-minute flight to Chicago?
It is possible to find cheap, last-minute flights to Chicago, especially if you can be flexible with your dates, times and route. Whether you're planning a spontaneous getaway or need to travel for business, there are plenty of last-minute flight deals on Expedia. You can also bundle your flight and hotel for even more savings with a package deal.
Can I earn miles booking a flight to Chicago with Expedia?
You can earn miles when booking a flight to Chicago on Expedia. Before confirming your booking, just select the frequent flyer program name and enter your program number. For even more rewards, join One Key™—our free travel rewards program. One Key members earn OneKeyCash™* on eligible bookings for every dollar spent.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
Can I save money by booking a Chicago trip package?
Book a Chicago flight and hotel package deal on Expedia, and you can make significant savings. It's simple to bundle your accommodations and flights, and you can also add car rentals and activities to create your own customized Chicago trip. Plus, nothing beats the convenience of booking everything in the same place.
Can I change or cancel my flight to Chicago?
It's often possible to cancel or change your flight to Chicago using Expedia. Many airlines let you cancel your flights for free within 24 hours of booking. However, some flights are non-refundable, and airlines may offer to reschedule your flight rather than provide a direct refund. To find affordable flights to Chicago with flexible change policies, select "No cancel fee" or "Changes included" when you search. Need more information? Visit our Customer Service Portal.

*Flight schedules are subject to change.

Flights to Chicago information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
$52

Trending flights to Chicago

Prices were available within the past 7 days and start at $26 for one-way flights and $52 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Mar 10 - Wed, Mar 11
EWR
New York
ORD
Chicago
$52 Roundtrip, just found
$52
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Mar 10 from New York to Chicago, returning Wed, Mar 11, priced at $52 just found

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